The Phillies’ Andrew Painter gamble looks worse every time his name comes up.
Philadelphia built a lot around the former top prospect, but the return has been ugly so far. Painter hasn’t looked the same since Tommy John surgery, and the concern around his long-term outlook is only getting louder.
The Phillies are stuck in a tough spot: they’ve already invested too much to move him at his lowest value, but they also can’t keep running him out there and sacrificing games. That’s why the 2021 draft keeps coming back into focus.
Five years is still a short window for a draft class. Plenty of those players are only now settling into the majors, and some still have room to grow into the stars teams hoped they’d become. But it’s enough time to see which picks are already paying off.
Painter’s case is especially painful because the Phillies had other options. He dominated minor league hitters before the surgery in 2023 wiped out that season and the next one.
When he returned in 2025, Triple-A hitters got to him. Even so, Phillies president of baseball operations Dave Dombrowski gave him a rotation spot on Opening Day this year, and that move quickly unraveled.
Painter was shelled to a 7.06 ERA in 14 appearances with the Phillies before getting sent back to Triple-A last month. His latest rough outing last Friday should make any quick return to the majors unlikely.
That leaves Philadelphia with a rotation problem that now has to be addressed at the trade deadline, and Painter’s struggles may end up costing the club prospect capital to fix it. So the obvious question hangs over the whole thing: who else was on the board in 2021?
A few names jump out immediately. The St.
Louis Cardinals got Michael McGreevy with the 18th overall pick, and he’s put together a 3.01 ERA in 18 starts this season. Two picks later, the Cleveland Guardians took Gavin Williams, who has a 3.81 ERA in 19 starts.
Either arm would look awfully useful in Philadelphia right now.
The regret doesn’t stop on the mound, either. The Phillies’ outfield remains a problem, and Brandon Marsh is the only player there who feels trustworthy.
Just two selections after Painter, the Milwaukee Brewers took Sal Frelick, who posted a .756 OPS in 142 games last season and won a Gold Glove Award in 2024. Then came Jackson Merrill, the 27th overall pick by the Padres.
The 23-year-old centerfielder has had a rough year, but he already owns an All-Star nod and a Silver Slugger Award, along with a career .264/.310/.446 line. Either one would have helped a lot.
Shortstop is another sore spot, even with Trea Turner still holding down the position. The 22nd pick in that draft, Colson Montgomery, debuted last season and has hit .228/.306/.469 over his first 162 big league games.
Catcher is no better. J.T.
Realmuto is no longer the player he once was, and the Phillies signed him to a three-year, $45 million deal last winter because they were desperate. The No. 31 pick, Joe Mack, might have changed that picture.
He hit 60 homers in the minors and has seven in 60 major league games.
The 2021 class may not end up producing a true franchise-defining superstar, but there’s been plenty of major league value in it. Painter just hasn’t been part of that group, and for the Phillies, that’s the painful part.
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Phillies Keep Facing One Rotation Problem They Cant Ignore
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Now the pressure is shifting from simply covering innings to finding a more reliable answer before the August 3 trade deadline. The club has already cycled through several options, including Taijuan Walker, Tim Mayza, Tanner Banks, Zach Pop and Kyle Backhus, while some possible internal reinforcements have already been removed from the 40-man roster. With the market thinning out and the calendar moving fast, the Phillies are left weighing how much longer they can afford to treat the fifth starter spot as a temporary fix. [Read more 🡒]